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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 523934Generated: October 30, 2026

Water → HCID 58545056, compound

https://huagongshe.com/reaction/523934

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantPotassium CarbonateHCID 11430—
Reactant4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 2734620—
ReactantHCID 86660147HCID 86660147—
CatalystHCID 178418397HCID 178418397—
SolventTolueneHCID 1140—
ProductHCID 58545056HCID 5854505670.1%

Reaction Steps

Compound II (52 mg, 0.109 mmol), Pd(PPh3)4 (12 mg, 0.011 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (48 mg, 0.218 mmol) and potassium carbonate (60 mg, 0.44 mmol) were stirred in toluene (3 mL) and water (1.5 mL) at 120° C. under microwave irradiation (300 W) for 30 min. The reaction mixture was then poured onto brine (50 mL) and extracted with EtOAc (2×20 mL). The organic phases were combined then dried over MgSO4, filtered, and subsequently evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting with hexane/EtOAc (90:10 then 0:100) to furnish III as a brown oil (32 mg, 70%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09340503B2
Source datasetuspto-grants-2016_05
ORD IDord-826947c4fb89450789dbd1d47423e582
Source noteuspto-grants-2016_05